“Come on, I dare you!” Jack teased Hadley. The couple was walking downtown, on their way to the car after a nice dinner. They had drunk a bit of wine and it had had an effect on them.
Hadley swatted at Jack’s arm. “No. When I mentioned that it was my fantasy to flash someone, that’s all I meant it to be – a fantasy. Nothing more, nothing less.”
She moved closer to Jack as they passed three rather rough-looking men on the sidewalk. She felt their eyes roving over her body and it bothered her.
Jack noticed their attentions also. Pulling her close, he whispered, “You know perfectly well how hot you are and what a huge thrill you would give those guys if you showed them your tits right now.” He started rubbing her ass through her silk skirt. “They would come immediately and you know how hot it gets me, knowing that everyone wants to fuck you and yet, you’ll still be mine.”
They stopped walking. Hadley glanced over and caught their reflection in the storefront. They made a nice couple, she thought. Hadley herself was a curvy girl, more voluptuous than society approved of, yet still shapely. Her straight blond hair fell halfway down her back and her green eyes always attracted people. Her tits nicely filled out her button down shirt. Jack was the typical “tall, dark and handsome” type; 6’5″ with a great head of dark, chocolate brown hair. They usually garnered lots of attention when they went out together.
Jack pulled her close, gripping her ass. She felt his fingers digging into the cleft between her cheeks, spreading her wide. She gasped and pressed herself against Jack. She opened her mouth to say something and his mouth pressed tight to hers. Her lips parted under his and he began to fuck her mouth with his tongue, driving his it deep inside. She gasped and arched against him. In addition to his tongue, she felt his hands lifting up her skirt, exposing her bare ass to the cool night air.
“Naughty bitch, not wearing any panties,” he said quietly. With one hand he held her skirt around her waist. He brought his other hand down rapidly and struck her ass sharply. This got the attention of the transients on the street. They stopped talking and began to watch the action.
Jack slapped Hadley’s ass again, this time raising a red mark. She moaned and pressed herself tighter against him, crushing her tits to his chest, feeling his growing cock against her stomach. He quickly turned her around, pressing her against the rough wall of the building.
Hadley turned towards him, “Jack, I don’t think this is such…” Her words trailed off as she watched him. He was slowing pulling his belt through the loops on his pants. Once it was free, he looped it over on itself, creating a very effective, makeshift flogger. With his other hand, he unknotted his tie. He moved closer to Hadley and motioned for her to open her mouth. He then shoved a good portion of the tie into her mouth, knotting the ends behind her head.
He placed her hands upon the wall, shoulder width apart. This forced her to slightly arch her back, thrusting out her newly reddened ass. Hadley was mortified by Jack’s behavior. They often engaged in role playing and harmless dominance at home, but this was definitely not their bedroom.
“Now, you little pussy, I’ll show you who’s in charge here,” Jack said softly. “If you move your hands, there’ll be hell to pay. You see those guys over there? If you don’t keep your hands right there, I’ll let them come over here and fuck all of your holes. Hell, even if you behave, I still might let them.” With that, he brought his belt straight down on her ass.
Hadley made a squeaking sound underneath the necktie. She felt Jack rubbing her ass, warming it up even more. The juices from her pussy were beginning to drip down her thighs. She felt eyes on her and looked over to her left. The transients were standing there, not even 10 feet away, watching everything. One of them had even pulled out his long, thin purplish cock and was vigorously jacking off. She closed her eyes as Jack began to spank her even harder, not allowing her to catch her breath between swats.
Suddenly, she felt a tongue on her pussy. Looking down, she was mortified to see one of the transients running his tongue up and down her lips. She was so embarrassed and yet so hot. The combination of his tongue and Jack’s spanking were really turning her on.
He pulled away and looked right into her eyes. “Damn, your pussy sure is juicy and smooth.” He put his hands on either side of her pussy, spreading her wide. He began to lick up and down her slit, from her asshole all the way to her clit. Hadley shivered each time his tongue grazed her clit.
Jack stopped spanking her ass. He leaned over her, pressing his hard cock into the crack of her ass. Reaching around, he pulled and twisted on her nipples, eliciting soft cries from her.
“You’re such a slut, Hadley,” he whispered. “Here you are, standing in the middle of downtown, getting spanked and eaten out by a fucking stranger! You love it don’t you?”
She nodded, incapable of speaking.
Jack stepped away, exposing her to the cold. The transient also moved away. Jack took Hadley’s hand in his and motioned for the transients to follow them. Jack led them all into a dark alley that smelled of stale urine and garbage.
“Now, I noticed you guys admiring my girl earlier. Not that I can blame you, she is a hot piece of ass. Tell me your names.”
The one that had been jacking off spoke first. “My name is Lloyd.” He was easily at least 60 years old and sounded as if he had smoked 5 packs of cigarettes a day for the majority of his life.
“I’m Sid,” said the second one. He still had a glaze of pussy juice on his thin face. He sounded as if he was foreign, but Hadley couldn’t be sure. He nudged the last one and said, “This here’s Steven. He’s a bit shy as he’s not been with a woman since he got out of prison.”
Hadley shivered. She didn’t want any of these men anywhere near her. She looked to Jack, who just laughed at her.
“Hadley, you’re going to fuck these nice men. And, knowing you, you’ll enjoy every minute of it.” With that, he turned to the men, “You can have your way with her. Her mouth and pussy are yours to use. And, you might be interested to know that she loves taking cock up her ass.” He stepped away, leaning against the wall as the transients came closer.
Hadley backed away. There was no way she was going to let them fuck her. She took three steps backward and met the wall. The men advanced on her. Sid reached forward and grabbed her shirt, ripping it open down the middle. Her tits spilled free, nipples hardening in the night air. He began to maul them, squeezing and kneading them. He lowered his head and began to nurse on her big tits, rolling her nipple between his teeth, biting and pulling it.
Against her better judgment, Hadley began to enjoy it. She arched her back, filling Sid’s mouth with her tit. He groaned around it. She started gently thrusting her hips, feeling her lips getting thicker and the juice running down her legs.
Lloyd got to his knees below her. Maintaining eye contact with her, he ran his tongue up her slit, slipping inside every once in a while to deeply tongue-fuck her pussy. Hadley felt her clit swelling – Lloyd’s teeth on her clit and Sid’s teeth on her tit were having the desired effect. She glanced to the side. Jack was standing there, against the rough brick wall, arms crossed, silently watching her. He nodded slowly and with that, Hadley knew not only that he wanted her to be a whore for him, but that he had this planned all along. She gave herself up to the experience.
Lloyd suddenly leaned backwards, pulling her down on top of him. She slid down and grabbed his erect cock. When he had been jacking off earlier, it hadn’t looked that impressive. But now, in her hand, it was exactly what she wanted. He grabbed her hips and slightly lifted her up. Hadley impaled herself on him and gasped with the intensity of having a total stranger’s cock inside her pussy.
Sid came over to stand in front of her. He had his right hand wrapped around his shaft and was rapidly stroking it to erection. With his left, he tore off the makeshift gag, leaving red welts on her face. His cock was a bit larger than Lloyd’s, larger even than Jack’s cock. He pinched her nose in between the fingers of his left hand, forcing her mouth to open. She opened as wide as she could and his cock slid straight down her throat, until his balls were resting against her chin. He began to fuck her mouth with long, even strokes.
Hadley started to ride Lloyd’s cock. Her pussy grabbed onto his cock as she bounced up and down, tits bouncing in rhythm with their fucking. Her clit was mashed against his pubic bone and her mouth was stretched wide around Sid’s thick cock.
Suddenly, she felt a hand on the back of her neck. She tried to turn around and couldn’t, not with Sid’s meat buried deep in her throat. Looking out the corner of her eye, she saw that Jack was still standing there, silently watching her degradation. That meant one thing: The hand her neck, forcing her down against Lloyd, belonged to Steven, The one who had just gotten out of prison.
Hadley began to struggle at that point. She didn’t want a former inmate using her body in any way. Everyone knows what happens in prison. She tried to get off of Lloyd, but his hands clamped down on her ass, spreading her cheeks while Sid pulled her hair and forced her mouth even deeper on his cock.
A voice in her ear whispered, “Go ahead and fight you bitch. I’ve always enjoyed fucking unwilling women. Why do you think I went to prison, anyway?”
With that, he thrust hard into her unprepared ass. She screamed around the cock in her mouth, but the only sound that came out was a muffled groan. Now all of her holes were filled with cock. They were filled with stranger cock, to be precise.
The men began to fuck her in three different rhythms. Her ass felt like it was on fire and Steven kept fucking her hard. Lloyd began to thrust up at her, meeting her downward thrusts. Sid kept his hands tangled in her hair, forcing her to suck his cock. She kept gagging but he didn’t care. It only seemed to excite him more.
Soon, something odd began to happen: Hadley began to enjoy it, even the brutal ass fucking she was getting from the former prisoner. Her nipples were hard enough to cut glass and her pussy was so wet a puddle was forming on the pavement beneath Lloyd. Her ass began to loosen up and the friction became pleasurable, not painful.
Without warning, she came. Her back arched, thrusting her full tits out in the night air. Her pussy clamped down on Lloyd’s cock, milking it of every drop of come. Lloyd’s skinny ass rose up off the pavement, shooting his load deep into her clenched pussy.
Sid was next to come with his cock buried balls deep in her throat. He held Hadley’s head hard to his groin as his hot come spurted deep in her throat. She gagged around his cock and come dribbled out of the corners of her mouth, splashing down onto her tits. He pulled his softening cock out of her mouth and wiped it clean on her cheeks, leaving them sticky and shiny.
That left Steven, who was still pumping her ass hard. Lloyd’s dick had gone completely flaccid and slipped out of her pussy. His limp cock was rubbing against her clit as her ass was getting pummeled. Her asshole had loosened up enough to where there was very little pain. Hadley felt Steven’s strong, calloused fingers digging into her hips. She concentrated on her timing her breathing to his thrusts, in and out, in and out.
The friction of Lloyd’s soft cock against her clit was edging her to another orgasm. Steven began to rhythmically slap her ass in time with the tempo of his fucking. Hadley gasped at the combination of pleasure and pain.
Steven pulled his cock out of her ass, grabbed her hair and forcibly turned her around to face him. Her vision was filled with the sight of his thick cock, which he was stroking right in front of her face. Suddenly, a fountain of thick come shot out, covering her face and dripping down her body. A few errant spurts landed in her hair. Still holding her hair, he drew her head down onto his cock.
“Suck it, bitch. Clean my cock,” he muttered.
She opened her mouth wide, tasting her ass and his come. She just concentrated on cleaning his cock as she wasn’t sure he was done with her just yet.
Stepping away from her, Steven zipped his pants back up. Hadley slumped over on the pavement, feeling come leaking out of all her holes. The transients walked off, each boasting about their conquest; they all sounded like cock-sure teenage boys.
Hadley has lost all sense of time during the gang bang and just lay there, reliving her shame; shame at having been forced to fuck three strangers – transients no less – and shame at having enjoyed their brutal assault.
Feet entered her line of sight. Looking up, Hadley saw Jack standing above her. Offering her his hand, he helped her to stand on shaky legs. Hadley wouldn’t meet his eyes; she was too embarrassed. During the gang bang, she had totally forgotten about him.
He cupped her chin in his hand, turning her face up to his. “That was wonderful, Hadley. I am so proud of you.” His other hand wandered down to her chest, where he rubbed in the remainder of the come. Handing her clothes to her, he helped her dress, which was no easy feat considering her blouse had been ripped off. She held the torn material around herself as she stepped into her skirt.
Jack took her arm and guided her out of the alley. “I think we’ll have to do this again next weekend.”
Hadley laughed softly, the sound a mixture of arousal and dread.